The present invention relates to novel pentafluorophenyl derivatives, methods of production thereof, and methods of optical resolution of chiral carboxylic acids.
A racemate and/or an optical active form of pentafluorophenyl derivatives in accordance with the present invention can be used suitably as derivatizing agents for electron capture detection and optical resolution for analysis and as intermediates for medicines, agricultural chemicals, functional polymers, etc.
Many fluorine-containing compounds which exhibit special physical properties and physiological activities are known. For instance, bromo(pentafluorophenyl)methane [Anal. chem., 40, 2073 (1963)] and 0-[(pentafluorophenyl)-methyl]hydroxylamine [J. chromatogr. Sci.), 13, 97 (1975)], both of which are pentafluorophenyl derivatives, can be used for sensitive analysis as electron capturing agents.
Among various pentafluorophenyl derivatives, 1-(pentafluorophenyl)ethanol is already known, and can be derived by reduction of methyl(pentafluorophenyl)ketone. In addition, an optical active one has been obtained by optical resolution or asymmetric reduction of methyl(pentafluorophenyl)ketone using optically active binaphthol. [Liebigs Ann. Chem., 1986, 2004]
However, the above-described optical resolution requires a special optical resolving agent and a complicated operation. On the other hand, the asymmetric reduction requires an expensive binaphthol as the chiral source. In addition, 2-fluoro-2-(pentafluorophenyl)ethanol and 1-(pentafluorophenyl)ethyl sulfonate are not yet known.
The present inventors found that 2,3,4,5,6-pentafluorostyrene oxide can be obtained via microbial epoxidation of 2,3,4,5,6-pentafluorostyrene (Japanese Patent Application No. 233497/1984).
The present inventors discovered novel pentafluorophenyl derivatives during the course of research concerning 2,3,4,5,6-pentafluorostyrene oxide, and found that these novel derivatives are optical active and can be suitably used particularly as derivatizing agents for electron capture detection and optical resolution for sensitive analysis, and as intermediates for medicines, agricultural chemicals, functional polymers, etc.
The present invention has been devised on the basis of this new knowledge.